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MedKoo Cat#: 462097 | Name: Kaitocephalin

Description:

WARNING: This product is for research use only, not for human or veterinary use.

Kaitocephalin is a non-selective ionotropic glutamate receptor antagonist, meaning it blocks the action of the neurotransmitter glutamate. It is produced by the fungus Eupenicillium shearii. Although similar molecules have been produced synthetically, kaitocephalin is the only known naturally occurring glutamate receptor antagonist.

Chemical Structure

Kaitocephalin
Kaitocephalin
CAS#198710-92-8

Theoretical Analysis

MedKoo Cat#: 462097

Name: Kaitocephalin

CAS#: 198710-92-8

Chemical Formula: C18H21Cl2N3O9

Exact Mass: 493.0655

Molecular Weight: 494.28

Elemental Analysis: C, 43.74; H, 4.28; Cl, 14.34; N, 8.50; O, 29.13

Price and Availability

This product is currently not in stock but may be available through custom synthesis. To ensure cost efficiency, the minimum order quantity is 1 gram. The estimated lead time is 2 to 4 months, with pricing dependent on the complexity of the synthesis (typically high for intricate chemistries). Quotes for quantities below 1 gram will not be provided. To request a quote, please click the button below. Note: If this product becomes available in stock in the future, pricing will be listed accordingly.
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Related CAS #
No Data
Synonym
Kaitocephalin; PF-1191
IUPAC/Chemical Name
(2R,5R)-2-((1S,2R)-2-amino-2-carboxy-1-hydroxyethyl)-5-((S)-2-carboxy-2-(((Z)-(3,5-dichloro-4-hydroxyphenyl)(hydroxy)methylene)amino)ethyl)pyrrolidine-2-carboxylic acid
InChi Key
AJQRDRIPQOAJCM-BWOKQULHSA-N
InChi Code
InChI=1S/C18H21Cl2N3O9/c19-8-3-6(4-9(20)12(8)24)14(26)22-10(15(27)28)5-7-1-2-18(23-7,17(31)32)13(25)11(21)16(29)30/h3-4,7,10-11,13,23-25H,1-2,5,21H2,(H,22,26)(H,27,28)(H,29,30)(H,31,32)/t7-,10+,11-,13+,18-/m1/s1
SMILES Code
N[C@H]([C@H](O)[C@]1(CC[C@H](C[C@H](NC(=O)c2cc(Cl)c(O)c(Cl)c2)C(=O)O)N1)C(=O)O)C(=O)O
Appearance
Solid powder
Purity
>98% (or refer to the Certificate of Analysis)
Shipping Condition
Shipped under ambient temperature as non-hazardous chemical. This product is stable enough for a few weeks during ordinary shipping and time spent in Customs.
Storage Condition
Dry, dark and at 0 - 4 C for short term (days to weeks) or -20 C for long term (months to years).
Solubility
Soluble in DMSO
Shelf Life
>3 years if stored properly
Drug Formulation
This drug may be formulated in DMSO
Stock Solution Storage
0 - 4 C for short term (days to weeks), or -20 C for long term (months).
HS Tariff Code
2934.99.9001
More Info

Preparing Stock Solutions

The following data is based on the product molecular weight 494.28 Batch specific molecular weights may vary from batch to batch due to the degree of hydration, which will affect the solvent volumes required to prepare stock solutions.

Recalculate based on batch purity %
Concentration / Solvent Volume / Mass 1 mg 5 mg 10 mg
1 mM 1.15 mL 5.76 mL 11.51 mL
5 mM 0.23 mL 1.15 mL 2.3 mL
10 mM 0.12 mL 0.58 mL 1.15 mL
50 mM 0.02 mL 0.12 mL 0.23 mL
1: The Structure of (−)-Kaitocephalin Bound to the Ligand Binding Domain of the (S)-α-Amino-3-hydroxy-5-methyl-4 isoxazolepropionic Acid (AMPA)/Glutamate Receptor, GluA2 Ahmed H. Ahmed, Makoto Hamada, Tetsuro Shinada, Yasufumi Ohfune, Laksiri Weerasinghe, Philip P. Garner, Robert E. Oswald J Biol Chem. 2012 Nov 30; 287(49): 41007–41013. Published online 2012 Oct 17. doi: 10.1074/jbc.M112.416362 PMCID: PMC3510803 2: Kaitocephalin Antagonism of Glutamate Receptors Expressed in Xenopus Oocytes Agenor Limon, Jorge M. Reyes-Ruiz, Rishi G. Vaswani, A. Richard Chamberlin, Ricardo Miledi ACS Chem Neurosci. 2010 Mar 17; 1(3): 175–181. Published online 2009 Dec 28. doi: 10.1021/cn900037c PMCID: PMC2860192 3: From Toxins Targeting Ligand Gated Ion Channels to Therapeutic Molecules Adak Nasiripourdori, Valérie Taly, Thomas Grutter, Antoine Taly Toxins (Basel) 2011 Mar; 3(3): 260–293. Published online 2011 Mar 21. doi: 10.3390/toxins3030260 PMCID: PMC3202823 4: Novel Phosphorylated Penta-1,4-dien-3-one Derivatives: Design, Synthesis, and Biological Activity Lijuan Chen, Tao Guo, Rongjiao Xia, Xu Tang, Ying Chen, Cheng Zhang, Wei Xue Molecules. 2019 Mar; 24(5): 925. Published online 2019 Mar 7. doi: 10.3390/molecules24050925 PMCID: PMC6429309 5: Electrophysiological evaluation of extracellular spermine and alkaline pH on synaptic human GABAA receptors A. Limon, E. Delbruck, A. Yassine, D. Pandya, R. M. Myers, J. D. Barchas, F. Lee, Schatzberg, S. J. Watson, H. Akil, W. E. Bunney, M. P. Vawter, A. Sequeira Transl Psychiatry. 2019; 9: 218. Published online 2019 Sep 5. doi: 10.1038/s41398-019-0551-1 PMCID: PMC6728327 6: Metal-Mediated Halogen Exchange in Aryl and Vinyl Halides: A Review Gwilherm Evano, Antoine Nitelet, Pierre Thilmany, Damien F. Dewez Front Chem. 2018; 6: 114. Published online 2018 Apr 26. doi: 10.3389/fchem.2018.00114 PMCID: PMC5932166 7: Studies toward the Total Synthesis of Itralamide B and Biological Evaluation of Its Structural Analogs Xiaoji Wang, Chanshan Lv, Junmin Feng, Linjun Tang, Zhuo Wang, Yuqing Liu, Yi Meng, Tao Ye, Zhengshuang Xu Mar Drugs. 2015 Apr; 13(4): 2085–2104. Published online 2015 Apr 13. doi: 10.3390/md13042085 PMCID: PMC4413201 8: Ligands for Ionotropic Glutamate Receptors Geoffrey T. Swanson, Ryuichi Sakai Prog Mol Subcell Biol. Author manuscript; available in PMC 2010 Jul 9.Published in final edited form as: Prog Mol Subcell Biol. 2009; 46: 123–157. doi: 10.1007/978-3-540 87895-7_5 PMCID: PMC2901239 9: Nitrenium Ion Azaspirocyclization-Spirodienone Cleavage: A New Synthetic Strategy for the Stereocontrolled Preparation of Highly Substituted Lactams and N-Hydroxy Lactams Duncan J. Wardrop, Matthew S. Burge J Org Chem. Author manuscript; available in PMC 2012 Mar 20.Published in final edited form as: J Org Chem. 2005 Dec 9; 70(25): 10271–10284. doi: 10.1021/jo051252r PMCID: PMC3308172 10: Recent Progress on the Stereoselective Synthesis of Cyclic Quaternary α-Amino Acids Carlos Cativiela, Mario Ordóñez Tetrahedron Asymmetry. Author manuscript; available in PMC 2010 Mar 16.Published in final edited form as: Tetrahedron Asymmetry. 2009 Jan 30; 20(1): 1–63. doi: 10.1016/j.tetasy.2009.01.002 PMCID: PMC2839256 11: Stereoselective Synthesis of Quaternary Proline Analogues M. Isabel Calaza, Carlos Cativiela European J Org Chem. Author manuscript; available in PMC 2009 Aug 3.Published in final edited form as: European J Org Chem. 2008; 20: 3427–3448. doi: 10.1002/ejoc.200800225 PMCID: PMC2719988 12: Anti-AIDS Agents 81. Design, Synthesis and Structure-Activity Relationship Study of Betulinic Acid and Moronic Acid Derivatives as Potent HIV Maturation Inhibitors Keduo Qian, Reen-Yun Kuo, Chin-Ho Chen, Li Huang, Susan L. Morris-Natschke, Kuo-Hsiung Lee J Med Chem. Author manuscript; available in PMC 2011 Apr 22.Published in final edited form as: J Med Chem. 2010 Apr 22; 53(8): 3133–3141. doi: 10.1021/jm901782m PMCID: PMC2860721